Generation of heterocyclic quinone methides from ortho-hydroxy methyl derivatives and a study of their cycloaddition reactions
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 8,p. 527-529
- https://doi.org/10.1039/c39880000527
Abstract
Quinolinone quinone methide (1a), prepared from 1,3-dimethyl-4-hydroxyquinolin-2-one and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ), gives a dimer (5) and reacts in situ with 2,2-dimethyl-2H-1-benzopyran, and with isopropenyl acetate, to give Diels–Alder cycloaddition products; coumarin quinone methides behave similarly with 2,2-dimethylbenzopyran, but with isopropenyl acetate and with 2,3-benzofuran give adducts that probably result from [2 + 2] cycloaddition reactions.Keywords
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